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A facile and efficient synthesis of Bis-thiazole from mono-thiazole

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Abstract

This paper describes a facile route for the synthesis of bis-thiazoles from mono-thiazole with an eco-friendly method. The synthetic procedure for the synthesis of bis-thiazoles from the reaction of 2-amino-4-tolyl thiazole with different aromatic aldehydes under microwave irradiations is discussed. Structures of the final products are characterized by IR, 1H and 13C- NMR spectra, DEPT-135 and mass spectrometry.

Graphical abstract

A facile method is developed to synthesis bis-amino thiazole from easily synthesised mono thiazole. A series of bis thiazole were obtained with free amino groups which can be used for late-stage synthesis of new bis heterocyclic compounds.

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References

  1. Nayak S and Gaonkar S L 2019 A review on recent synthetic strategies and pharmacological importance of 1,3-Thiazole derivatives Mini-Rev Med. Chem. 19 215

    Article  CAS  Google Scholar 

  2. Ayati A, Emami S, Asadipour A, Shafiee A and Foroumadi A 2015 Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug Discovery Eur. J. Med. Chem. 97 699

    Article  CAS  Google Scholar 

  3. Siddiqui N, Arya S K, Ahsanb W and Azad B 2011 Diverse biological activities of thiazoles: a retrospect Int. J. Drug Dev. Res. 3 55

    CAS  Google Scholar 

  4. Metwally M A, Abdel-Latif E, Amer F A and Kaupp G 2004 Versatile 2-amino-4- substituted-1,3-thiazoles: synthesis and Reactions J. Sulfur Chem. 25 63

    Article  CAS  Google Scholar 

  5. Das D, Sikdar P and Bairagi M 2016 Recent developments of 2-aminothiazoles in medicinal chemistry Eur. J. Med. Chem. 109 89

    Article  CAS  Google Scholar 

  6. Khalifa M E 2018 Recent developments and biological activities of 2-aminothiazole derivatives Acta Chim. Slov. 65 1

    Article  CAS  Google Scholar 

  7. Tsai C Y, Kapoor M, Huang Y P, Lin H H, Liang Y C, Lin Y L, et al. 2016 Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents Molecules 21 145

    Article  Google Scholar 

  8. Chen B C, Zhao R, Wang B, Droghini R, Lajeunesse J, Sirard P, Endo M, Balasubramanian B and Barrish J C 2010 A new and efficient preparation of 2- aminothiazole-5-carbamides: applications to the synthesis of the anti-cancer drug dasatinib Arkivoc vi 32

  9. Franklin P X, Pillai A D, Rathod P D, Yerande S, Nivsarkar M, Padh H, et al. 2008 2-Amino-5-thiazolyl motif: a novel scaffold for designing anti- inflammatory agents of diverse structures Eur. J. Med. Chem. 43 129

    Article  CAS  Google Scholar 

  10. Gupta R, Fuloria N K and Fuloria S 2013 Synthesis and antimicrobial profile of some newer 2-amino-thiazole derivatives Turk. J. Pharm. Sci. 10 425

    CAS  Google Scholar 

  11. Sharshira E M and Hamada N M 2012 Synthesis, Characterization and Antimicrobial Activities of Some Thiazole Derivatives Am. J. Org. Chem. 2 69

    Article  CAS  Google Scholar 

  12. Annadurai S, Martinez R, Canney D J, Eidem T, Dunman P M and Gharbia M A 2012 Design and synthesis of 2-aminothiazole based antimicrobials targeting MRSA Bioorg. Med. Chem. Lett. 22 7719

    Article  CAS  Google Scholar 

  13. Sravanthi T V, Pottem M R and Manju S L 2013 Design and Synthesis of BisThiazol- 2-ylidenes Asian J. Chem. 25 5370

    CAS  Google Scholar 

  14. Sayed A R 2015 Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates and bis- triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones Turk. J. Chem. 39 600

    Article  CAS  Google Scholar 

  15. Gomha S A, Farghaly T A and Sayed A R 2017 Design, Synthesis, and Characterization of Some New bis-thiazoles J. Heterocycl. Chem. 54 1537

    Article  CAS  Google Scholar 

  16. Khrustalev D P 2009 Modification of 2-amino-4-phenylthiazole under microwave irradiation Russ. J. Gen. Chem. 79 515

    Article  CAS  Google Scholar 

  17. Abdallah M, Defrawy A M E l, Zaafarany I A, Sobhi M, ElwahyA H M and Shaaban M R 2014 Inhibition effects and theoretical studies of synthesized novel bisaminothiazole derivatives as corrosion inhibitors for carbon steel in sulphuric acid solutions Int. J. Electrochem. Sci. 9 2186

    Google Scholar 

  18. Shawali A S 2016 Bis-hydrazonoyl halides: recent advances in their synthesis and their diverse synthetic applications leading to bis-heterocycles of biological interest J. Adv. Res. 7 873

    Article  CAS  Google Scholar 

  19. Turan-Zitouni G, Altintop M D, Ozdemir A, Kaplancikli Z A, Ciftci G A and Temel H E 2016 Synthesis and evaluation of bis-thiazole derivatives as new anticancer Agents Eur. J. Med. Chem. 107 288

    Article  CAS  Google Scholar 

  20. Dessi A, Calamante M, Mordini A, Zani L, Taddei M and Reginato G 2014 Microwave-activated synthesis of thiazolo[5,4-d]-thiazoles by a condensation/oxidation sequence RSC Adv. 4 1322

  21. Kumar Baba N H, Ashok D, Rao B A, Sarasija M, Murthy N Y S, Srinivasarao V and Parthasarathy T 2017 Microwave–assisted synthesis of bis(N-substituted thiazol-2- amine) derivatives and their biological activities Heterocycl. Commun. 23 405

    Google Scholar 

  22. Arab-Salmanabadi S 2017 Synthesis and Spectral Characterization of Novel Bis- thiazole Derivatives via Ring Closure of Benzo[d]thiazol-2-amine, Various α- Haloketones, and S-Nucleophiles J. Heterocycl. Chem. 54 3600

    Article  CAS  Google Scholar 

  23. Al-Omair M A, Sayed A R and Youssef M M 2018 Synthesis and Biological Evaluation of Bisthiazoles and Polythiazoles Molecules 23 1133

    Article  Google Scholar 

  24. Borde R M, Jadhav S B, Dhavse RR and Munde A S 2018 Design, Synthesis, and pharmacological evaluation of some novel Bis-thiazole derivatives Asian J. Pharm. Clin. Res. 11(4) 164

    Article  Google Scholar 

  25. Kumar Baba N H, Ashok D, Rao B A, Sarasija M and Murthy N Y S 2018 Microwave assisted synthesis and biological activity of novel bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole}derivatives Russ. J. Gen. Chem. 88 580

    Article  CAS  Google Scholar 

  26. Mekky A E M and Sanad S M H 2019 Microwave-Assisted Synthesis of Novel Bis(thiazoles) Incorporating Piperazine Moiety J. Heterocycl. Chem. 56 1560

    Article  CAS  Google Scholar 

  27. Mahmoud H A, Kassab R M and Gomha S M 2019 Synthesis and characterization of some novel bis-thiazoles J Heterocyclic Chem. 56 3157

    Article  CAS  Google Scholar 

  28. Mahmoud H K, Abbas A A and Gomha S M 2021 Synthesis, Antimicrobial Evaluation and Molecular Docking of New Functionalized Bis(1,3,4-Thiadiazole) and Bis(Thiazole) Derivatives Polycycl. Arom. Comp. 41 2029

  29. Metzger J V 1984 In Comprehensive Heterocyclic Chemistry R Katritzky and C W Rees (Eds.) (Oxford: Pergamon Press) Vol. 6 p. 235

  30. Shockravi A, Sadeghpour M and Olyaei A 2010 Simple and efficient procedure for the synthesis of symmetrical Bis-Schiff bases of 5,5’-methylenebis(2-aminothiazole) under solvent free conditions Synth. Commun. 40 2531

    Article  CAS  Google Scholar 

  31. Zav’yalov S I, Kravchenko N E, Ezhova G I, Kulikova L B, Zavozin A G and Dorofeeva O V 2007 Synthesis of 2-aminothiazole derivatives Pharm. Chem. J. 4 105

    Article  Google Scholar 

  32. Hantzsch A and Weber J H 1887 Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe) Ber. Dtsch. Chem. Ges. 20 3118

    Article  Google Scholar 

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Acknowledgements

I am thankful to the UGC, New Delhi, India, for financial support under College for Potential and Excellence research Grant. I acknowledge the guidance and support provided by Dr. Dharminder Singh Ubha, Principal, G.S.S.D.G.S. Khalsa College, Patiala.

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Correspondence to Monika Bansal.

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Bansal, M. A facile and efficient synthesis of Bis-thiazole from mono-thiazole. J Chem Sci 134, 36 (2022). https://doi.org/10.1007/s12039-022-02030-8

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